An Uptight Girl Learns to Relax - Part 6

Click here to read the previous parts of the story.

Julia has followed through on Ian's request and used a strapon on her boyfriend. She's made him take it. She's shown him the joy of surrendering to her. Now, as was promised, Julia is going to use the strapon on Ian. She's going to reverse their roles and have her way with him and he's not sure he's ready for it.

---

"I hope you're ready to get fucked."

Ian wasn't ready, but he was fairly certain that no straight man was ever truly ready to get fucked in the ass. He hadn't really expected Julia to follow through and fuck her boyfriend Mark with a strapon, so there was no reason to prepare.

"How do I know you actually fucked him?" he texted.

"I filmed it. I'll show it to you when I get to your place. Are you free tonight?"

"You really want to fuck me, don't you?"

"I think you need it, Ian. You need to surrender. You need to loosen up. You need to know what it's like to be bent over and pounded from behind. Your hole needs to be the source of someone's pleasure. And yes, I really want to fuck you," Julia texted.

A picture came through soon after. A mirror selfie. Julia had the phone in front of her face, but it was her. He recognized her breasts and the small birth mark on her thigh. He didn't recognize the strapon she was wearing, though. It was shaped like a real cock - mushroom head and all - but it was purple. It was above average in size - compared to most men, at least - and it glistened with some sort of lube.

"You opened me up in more ways than one, Ian. You've had all my holes multiple times. You've shown me the joys of sex in ways no man ever has. You've changed me for the better. I'm going to try and do the same for you with my cock."

"Do you think you changed Mark?"

"Time will tell. He liked getting fucked, though. It took a week of orgasm denial to get him to a place where he was horny enough to let me fuck him, but he liked it. He was nervous at first, but he warmed up to it, to the sense of surrender I always feel when you fuck me, Ian. Mark felt that and he liked it. He liked giving me his ass. He liked getting pounded. He liked hearing me moan - my strapon has a little nub that rubs against my clit - as I fucked him. He liked that I came while I was inside him. He liked that I kept on fucking him while jerking him off, too, and I'm damn sure he liked having an orgasm with my cock in his ass."

Ian had never thought of himself as the kind of man that would enjoy that sense of surrender. He'd always been the one on the other side of that equation and he'd always gotten off on that. He couldn't help his curiosity, though, and there was no denying the arousal gathering in his loins.

"So, are you free tonight?"

"I'm on a date, actually. She stepped away to the bathroom," he replied. "I took her to dinner. Now we're at a cocktail bar. She's an elegant woman. The kind that's into the finer things in life. She's going to enjoy the finest cock in the city tonight as soon as we finish our drinks, though the sex won't be as elegant and high-minded as I'm sure she's used to. Luckily, she'll have better orgasms than she usually does."

"You're such an asshole," Julia texted back.

"Yes, and I'll bet you're jealous that it's not you that's going to spend the night with my cock exploring your holes."

She offered no response.

"I'm free tomorrow night, though," he texted. "Tonight, though, I want you to use that dildo on yourself. Spread your legs and pound your pussy with it while you think about me fucking someone else's tight pussy. Think about someone else pleasuring me the way you want to pleasure me. Cum while you're awash in jealousy, Julia. Surrender to it. Then you can work out all of those complicated feelings tomorrow night when you try and show me that you can fuck me in the same way I fuck you."

"Go fuck yourself."

Ian smiled. Her anger was almost certainly real. He knew she'd do what he wanted, though. She liked doing as he instructed when it came to sex. She got off on it, in fact. Ian wondered if he'd feel the same way when the tables were turned tomorrow night.

"Hey, welcome back," he said as his date returned from a trip to the bathroom.

She sat across from him, leaned forward enough to flash her incredible cleavage - no doubt on purpose - and unleashed a smile that made it clear she was ready to go home with him.

"What do you say we finish our drinks and get out of here?" he suggested.

"I'd like that."

Soon enough she'd be on her knees with his hands in her hair and his cock in her throat. They'd use each other for a night, reaching heights of pleasure that few people ascended to. He'd fuck her again the next morning, too, rolling her onto her stomach in his bed and pounding her in that beautiful position while rubbing her clit, leading to the kind of thunderous orgasm that would leave her so exhausted she might just fall right back to sleep.

It was going to be a good night.

---

"Did you fuck yourself last night?" Ian texted the next morning with his date still fast asleep next to him.

"I did," Julia replied. "Did you have a good time with whatever whore you brought home?"

Her jealousy delighted him. "I did. I fucked her three times. She said she's never cum that hard before. Pretty soon she's going to wake up and I'll bet she crawls between my legs and sucks my dick to thank me for last night. I'll fuck her, of course, as a way of thanking her for being such a hot piece of ass."

"You're a pig."

"And you wish you were the one in my bed."

"Fuck you."

"I want a picture of your pussy. Right now. Spread your lips. Show me that I'm right, Julia. That you're thinking about me. That you wish you were waking up next to me after a night of taking my dick like a good girl. Show me that you'd prefer to wake up next to me instead of your boyfriend, that you'd prefer to suck my cock and then beg me to fuck you, to pound you, to make you cum, to cum inside you."

His dick was half hard as Ian realized that he too wished that Julia was the one in bed next to him.

She sent the picture not long after. It was clearly taken under the covers. She'd used the flash, though, and her pussy was exceptionally wet.

"I'll see you at seven o'clock sharp," Julia said. "Be cleaned, lubed, and ready because I'm going to fuck you hard, Ian."

He set his phone aside and smiled. His date stirred. She rolled towards him. Her hand rested on his chest and her lips found his cheek. She wished him a good morning and stroked his cock, noting that he was already hard for her. She didn't need to know that it was Julia he was hard for.

Not long after Ian's cock was in his date's mouth. He thought of Julia - of Mark's girlfriend - giving him head. He got hard as a rock. He put on a condom, rolled his date onto her stomach, and fucked her vigorously from behind while she moaned into the pillow, her pleasure reaching a crescendo as she experienced a wild climax that left her body trembling.

He came too, of course, doing so while he thought of fucking Julia and of getting fucked by her. It was a strange way to climax, but Ian couldn't ignore the thrill of it. His date seemed to notice, too, as she smiled brightly when he pulled out and rolled onto his back next to her.

As they cuddled, he wondered if he'd actually enjoy getting fucked or if he was merely taken with the notion of Julia turning the tables, of her confidence having grown so significantly that she was now ready to take control, to dominate, to show him what it was like to be penetrated, to be filled, to be fucked until the person inside you had a mind-bending climax.

In less than 12 hours Ian would know exactly how he felt about getting fucked by a woman.

---

Julia arrived in a pretty yellow dress and a white cardigan sweater. She wore her glasses and her hair was pulled into a ponytail. She looked like the woman she used to be, the uptight girl that had undergone a sexual awakening with Ian. Julia was no longer that girl, though, even though she still dressed like her.

She pushed into his apartment the moment he opened the door. Her tongue was in his mouth not long after as she loosened his belt and pushed his pants to the floor. She didn't go for his cock, though. Instead, she grabbed his ass and gave it a few hard smacks. She lowered his underwear and spread his cheeks. Her finger danced over his asshole and he tensed up.

"You'll need to learn to relax, Ian," she said. "Otherwise it's going to hurt when I fuck you."

"Damn...I'd say your transformation is complete, Julia."

She couldn't help but smile. She stepped back and adjusted her glasses before loosening her ponytail and letting her blonde hair cascade over her shoulders. "You think so?"

"I mean, I guess we're all transforming all the time, but the person you were six months ago is nothing like the person standing in front of me right now, at least where sex is concerned."

Julia stepped closer, but this time she offered a simple kiss on the cheek. "I'm grateful for that, Ian. I like the person I am, sexually speaking. I'm a great deal more satisfied. I'm a great deal happier, too. More confident on top of all of that. I have no interest in being a shrinking violet anymore."

He reached for her waist and pulled her close to try for a real kiss, but Julia slipped from his grasp.

"I want you naked and on your knees when I get back."

She walked away, disappearing into his bathroom and locking the door behind her. Ian had agreed to let Julia fuck him and he felt no particular desire to resist her instructions, so he stripped, stroked his cock a little, and then got on his knees in the living room.

When Julia emerged, her hair was pulled into a high, tight ponytail. Her glasses were gone and she'd put on dark red lipstick. She wore a black lace bra, matching black lace boyshorts, and her purple strapon. She looked like an entirely different woman than the one that had showed up at his door just a handful of minutes ago and Ian's jaw dropped.

"What do you think?" she asked.

"You're gorgeous."

Julia strode towards him and Ian took note of the leather ankle boots that might have been the sexiest part of her outfit. Then she was standing in front of him with her fingers around her cock. She stroked it slowly as he stared before directing his gaze upwards.

While stroking, she grabbed her phone from her bag and pulled up the video she’d promised to show him. The camera was off to the side of the bed and Ian guessed that Mark had no idea he was being filmed. He was, however, being fucked. There was no question about it. He was lying on his stomach and moaning with Julia taking him from being with slow, deep thrusts.

“I’m honestly a little bit surprised you actually did it,” Ian said.

She tossed the phone aside and smiled.

"I thought about making Mark suck my cock before I fucked him, but I don't think he would have done it. He would have felt too self-conscious, too afraid of what it might have meant, too nervous to look up at me while my cock entered the back of his throat. It's one thing to get fucked from behind, it's another thing entirely to look in the eyes of the person wielding the cock that's violating your mouth."

Ian opened his mouth to say something but Julia cut him off by sliding her strapon past his lips and putting a hand on the back of his head.

"No talking," she said. "Just suck."

He wrapped his lips around her dick and sucked. It was the first time he'd had a phallus in his mouth and the unfamiliar nature of the experience filled him with a sudden sense of insecurity, mostly because he had no idea what he was doing. He sucked. He moved his tongue over the head of the rubber cock. He tried to look up at her, too, though it proved difficult to maintain eye contact and suck cock at the same time.

"It's not that easy to be a cocksucker, is it?" she asked.

He shook his head.

"Don't worry, Ian. You'll get better. You'll learn how to please my cock. You'll learn not to gag when I push into your throat."

With a sudden thrust her strapon hit the back of his throat and he gagged, his stomach lurching painfully as he backed away and then leaned forward while trying not to vomit.

Before he'd fully recovered, Julia grabbed a handful of his hair, pulled back until it hurt, and directed her cock back into his mouth. She refrained from making Ian gag, though, letting him suck at his preferred pace while her face lit up with a kind of delighted arousal he wasn't sure he'd seen before.

"You're a terrible cocksucker, Ian," she said. "Everyone is their first time. I can tell that you're dedicated to my pleasure, though, that you want to make me feel good, that you're going to be willing to work to make yourself into a world class cocksucker for me. I can tell that you'll work at it until you can deepthroat me with ease."

Julia was repeating Ian's words - or a version of them - back to him. She was doing so with complete confidence, too, and her arousal was obvious. She was in her element, a once shy and reserved woman now blossomed into a sexual goddess of sorts, happily fucking his mouth with her strapon while holding a tight, controlling grip on his hair.

The blowjob went on long enough that Ian's throat and jaw ached by the time Julia pulled back, wrapped her fingers around her spit-soaked shaft, and moaned. Her chest was flushed red and her nipples were hard enough to poke through the delicate lace of her top. Her eyes were alive with desire, too, and Ian was surprised to find that he was sporting an erection. The effort required to give the blowjob had distracted him from the arousal that had flooded his body.

"I'm so fucking turned on," he said.

"So am I," Julia replied. "More than I thought I'd be, if I'm being honest. I want to fuck you, Ian. I want to put you on your hands and knees and fuck you hard. I want to cum while I fuck you."

"Please, Julia, fuck me."

He wanted it. Before he'd been merely willing to do it, but now Ian wanted it. He wasn't sure why, but he wanted it.

"Yeah? You want me to fuck your ass, Ian? You want me to slide my fat cock up your ass and fuck you like a bitch?"

"Yes, please," he begged. "Please, Julia, fuck me."

She laughed and then bent over and kissed him with surprising passion. Julia helped Ian to his feet, brought him to the couch, and put him on his hands and knees. She spanked his ass a handful of times, eliciting a painful yelp each time her hand struck his bare flesh. Then she spit on his asshole and rubbed it around. She spit in her hand, too, stroking herself to coat every inch of her cock in her saliva.

Ian sucked in a sharp breath when he felt the head of her dick push against his asshole. "Oh, fuck."

She kept pushing. The head popped past his anal ring and moved deeper. The shaft slowly stretched out his asshole, though it hurt. There was no question it hurt. Ian wished he'd worked with a butt plug beforehand to loosen himself up, but there was no fixing that oversight.

"How does it feel, bitch?"

"It hurts."

She smacked his ass and his anus clamped down on her dick. She pulled out and Ian felt even more pain. He closed his eyes and took a deep breath to try and relax. The strapon slid into him.

"Fuck this feels good," she said. "I took Mark while he was on his stomach. I should have made him get on his hands and knees so I could fuck him like a bitch. It feels so much better."

Ian reached back to stroke his dick. He wasn't sure why, but it felt good to know that Julia was enjoying herself. Really fucking good. "Harder. Please, fuck me harder."

She ran her hand up his back and grabbed a tight fistful of his hair. She pulled and he arched his back. The strapon suddenly felt better as she fucked him, as if a simple change in posture made the penetration easier. Ian began to move his hips back to meet her thrusts, to swallow her cock. He stroked himself faster, too, and his cock felt alive with desire.

"Don't you dare fucking cum," she said. "I will beat your ass red."

He released his dick and she fucked him harder. Julia was getting close. Ian could tell. He knew the rhythm. He recognized the heavy breathing. She put both hands on his shoulders for even better leverage. She was lost in the pursuit of her orgasm. She didn't give a shit about anything other than cumming. He was just a fuck hole in that moment. Her fuck hole.

"Oh, fuck!" Julia cried out.

She pushed every inch inside him and fell forward. Her body trembled as the soft lace of her bra pressed against his back. She kissed his flesh wherever her lips could find it and stroked his cock a little, keeping him in a state of intense desire as he felt a rush of satisfaction at having made her cum.

Julia pulled out and stepped back.

"Masturbate and cum on my cock," she said.

Ian backed off the couch and turned to face her. She smiled as he stroked his dick. She put her fingers in his mouth and called him names. She gently slapped his face a few times, which proved strangely exciting.

"I'm cumming!"

He blew his load on her strapon, coating the top in his seed. Some of it dripped onto the floor and some landed on her stomach, but most of it was on her rubbed cock.

"Back on your hands and knees," she instructed.

Ian knew what was coming. He'd been drained of his arousal, but that didn't stop him from smiling at how inventive Julia was. He moved to his and knees on the couch. She slid her strapon into his ass with ease. She filled him with his cum. She came in his ass.

Julia fucked him hard and had a second orgasm in almost no time. She pulled out and wiped the errant cum from his ass with his underwear. She stepped out of her strapon, leaving her in a bra, panties, and boots in his living room.

"I'd like a drink," she said. "Feel free to make one for yourself."

"You're incredible, Julia. In every fucking way."

A bright smile greeted his response before Ian headed for the kitchen to make drinks. He returned with cocktails in his hand and set them on the coffee table before moving towards the bedroom to retrieve a pair of fresh underwear.

"No," Julia said. "Sit naked. I'm going to fuck you again before the night is over. Missionary, I'm thinking. There's no point in getting dressed."

Ian sat next to her. She kissed him. She rested a hand on his leg. They enjoyed their cocktails.

He put on a movie, though they mostly ignored it in favor of conversation. Ian asked about Julia's work with the orchestra and she informed him of an impending promotion to first chair. She attributed her good fortune to her recent boost in confidence and rewarded Ian with a long, deep kiss soon after doing so.

"You're good for me, it turns out," she said.

"You're good for me too."

She stared into his eyes for a surprisingly long time and then kissed him on the cheek. Her lips lingered there for a few moments before she rested her head on his shoulder.

"I'd like to be your girlfriend, Ian," Julia said without preamble or fanfare.

"I'd like that too," he answered without hesitation, as if it was strange that she wasn't already his girlfriend.

As it turned out, though they might not have seemed like it at first glance, they were right for each other. Perfect for each other, even, which is why Julia broke up with Mark the next morning and started dating Ian seriously, starting a long and beautiful relationship that would make them both impossibly happy.

It wasn’t a fairytale romance, but it was theirs, and it was perfect in its own way.

The End.